6-O-(13-methyltetradecanoyl)-6'-O-oleoyl-α,α-trehalose | 1320208-40-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6-O-(13-methyltetradecanoyl)-6'-O-oleoyl-α,α-trehalose
• 英文别名: 6-O-(13-methylmyristoyl)-6’-O-oleoyltrehalose；6-O-(13-methylmyristoyl)-6'-O-oleoyltrehalose；maradolipid 15:0/18:1；maradolipid；[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(13-methyltetradecanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (Z)-octadec-9-enoate
• CAS: 1320208-40-9
• 化学式: C₄₅H₈₂O₁₃
• 分子量: 831.138
• InChiKey: PVZKDYANFLTWOS-CUNMKMKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  58
• 可旋转键数：
  35
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  海藻糖 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 195.13h， 生成 6-O-(13-methyltetradecanoyl)-6'-O-oleoyl-α,α-trehalose
  参考文献：
  名称：

  Synthesis of Ten Members of the Maradolipid Family; Novel Diacyltrehalose Glycolipids from Caenorhabditis elegans

  摘要：

  本文介绍了从三卤糖开始的直接合成马拉多脂家族十个成员的方法。

  DOI：

  10.1055/s-0030-1260318

文献信息

• Synthesis of Maradolipid
  作者：Vikram A. Sarpe、Suvarn S. Kulkarni

  DOI：10.1021/jo200979n

  日期：2011.8.19

  from C. elegans, is accomplished in five steps starting from trehalose in 45% overall yield. The short synthesis relies on dissymmetrization of trehalose core via regioselective acylation of a 2,3,4,2′,3′,4′-hexa-O-TMS trehalose 6,6′-diol derivative as a key step.

  从海藻糖中分离出的独特的不对称的6,6'-二-O-酰化海藻糖糖脂，从海藻糖开始，总产率为45％，分五个步骤完成了它的首次合成。短合成依赖于通过关键的步骤，通过2,3,4,2'，3'，4'-六-O -TMS海藻糖6,6'-二醇衍生物的区域选择性酰化对海藻糖核心进行不对称化。
• Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals
  作者：Vikram A. Sarpe、Suvarn S. Kulkarni

  DOI：10.1039/c3ob41389f

  日期：——

  Trehalose dibenzylidene and substituted dibenzylidene acetals were reductively opened either at O6 or O4 in a regioselective manner by using a DIBAL stock solution prepared in toluene or dichloromethane, respectively, to achieve desymmetrization of the trehalose core. The method was applied to synthesize various biologically important unsymmetrically substituted trehalose glycoconjugates, including

  使用在水中制备的DIBAL储备溶液，以区域选择性的方式在O6或O4处还原海藻糖二苄基和取代的二苄基缩醛。 甲苯 或者 二氯甲烷分别实现海藻糖核心的去对称化。该方法被用于合成各种生物学上重要的不对称取代的海藻糖糖结合物，包括分枝杆菌三糖，4-表位-海藻糖类似物和马拉多脂。
• Synthesis of a maradolipid without using protecting groups
  作者：René Csuk、Andrea Schultheiß、Sven Sommerwerk、Ralph Kluge

  DOI：10.1016/j.tetlet.2013.02.076

  日期：2013.5

  A convenient route has been developed to synthesize 6-O-mono- and 6,6'-di-O-acyl symmetrical and unsymmetrical (un)-symmetrically trehalose derivatives from trehalose using a combination of enzymic and nonenzymic reactions. Thus, a typical maradolipid was accessed in two-steps. (C) 2013 Elsevier Ltd. All rights reserved.
• Direct Synthesis of Maradolipids and Other Trehalose 6-Monoesters and 6,6′-Diesters
  作者：Nawal K. Paul、Jean-d’Amour K. Twibanire、T. Bruce Grindley

  DOI：10.1021/jo302231v

  日期：2013.1.18

  It was shown that reaction of trehalose with 1 equiv of a fatty acid in pyridine promoted by 1 equiv of the uronium-based coupling agent 2-(1H-benzotriazole-1-y1)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) at room temperature gives a good yield of the primary ester accompanied by small amounts of the diprimary ester using hexanoic, palmitic, and oleic acids as examples. Reactions using 2 equiv of the fatty acids gave the symmetrical diesters. The monoesters were reacted with different fatty acids to give nonsymmetric 6,6'-diesters in very good yields. Compounds synthesized include the most abundant component of the very complex maradolipid mixture, 6-O-(13-methyltetradecanoyl)-6'-O-oleoyltrehalose, and a component potentially present in this mixture, 6-O-(12-methyltetradecanoyl)-6'-O-oleoyltrehalose, a derivative of an ante fatty acid. The CS-C6 rotameric populations of 6-O-monoesters, symmetrical 6,6'-diesters, and 2,6,6'-triesters of fatty acids were calculated from the values of the H5-H6R and H5-H6S coupling constants and found to be similar to those found for glucose. The rotameric populations of the monosubstituted glucose residues in the 2,6,6'-triesters was altered considerably to favor the gt rotamer, presumably because of attraction between the 2- and 6'-fatty acid chains.
• Synthesis of Ten Members of the Maradolipid Family; Novel Diacyltrehalose Glycolipids from Caenorhabditis elegans
  作者：Teymuras Kurzchalia、Hans-Joachim Knölker、Ulrike Pässler、Margit Gruner、Sider Penkov

  DOI：10.1055/s-0030-1260318

  日期：2011.10

  The synthesis of ten members of the maradolipid family is described using a direct route starting from trehalose.

  本文介绍了从三卤糖开始的直接合成马拉多脂家族十个成员的方法。